The year 1968 saw plenty of upheaval in America and also on Mad Men, with things changing socially, politically, professionally, and personally. And yet the sixth season ended with many of the AMC drama's characters appearing to accept the cards they’d been dealt. Don stops trying to repress the ugly truths lurking of his past. Peggy loses her chance to be with Ted, but doesn’t seem to mind working through Thanksgiving in Don’s spacious office. Pete finds his freedom, even if it comes at an unforeseen cost. Megan finally stops denying how little she means to Don. But Mad Men creator Matthew Weiner cautions viewers not to get too hopeful about these various developments as we head toward the show’s end. As we begin to process the show's sixth season in the wake of Sunday's finale, Vulture called Weiner to ask about what that last scene in front of his childhood home might mean for Don’s future and to address the criticism directed that his lead character seemed to be stuck in a holding pattern. In the lengthy interview, Weiner also shared his thoughts on the many conspiracy theories that cropped up this season and what his original designs were for Bob Benson.

You said after last year’s finale that the lyrics to Nancy Sinatra’s song “You Only Live Twice,” which played over the end credits, held the key to understanding the entire fifth season. This year ended with Joni Mitchell's “Both Sides, Now,” which would fit lyrically with Don's reconciliation with his past. Did you know going in that you’d be capping the season with that song?No, I didn't — and it is the popular version from that period, which is Judy Collins's version of the song. I didn't know about the song itself until probably when I was writing episode nine or ten, so I was pretty deep in. But I knew that this whole season was about — and you can tell from the way we laid the children into it and the way that the premiere starts — Don and [the idea that] if he couldn't change, he could at least have a moment of reconciliation, of recognition. I at least knew from the beginning that he was going to tell a true story in that pitch, in an inappropriate place. And I knew that he was going to reveal to his children, and Sally in particular, after what has happened with Sally, where he grew up, that he was going to make that tiny gesture, which is a huge thing for him.

Will it make things better for him? Professionally, he took a big hit.Yeah. He's given some hits, too. I know that that [ejecting Don] seems like a very dramatic conclusion to the season, but let's look at his behavior. No matter how much of a genius you are, when you dump the biggest client, force your agency to merge, and then attack the people you merge with and withdraw from the business completely, you are a liability. You saw that in episode twelve when he's really trying to kill Ted — that's not someone you want to tolerate. And then, of course, the Hershey pitch being just the climax to a season of inappropriate behavior business-wise. But, you know, like I said from the opening, there's a lot about the children and those last moments with Roger and Kevin and Joan, and Roger and Margaret, and Pete and Tammy, and then Don. All the conversations …

At the start of the season, Jon Hamm said this year would be about Don needing to fix his foundation.Right. The idea was, whether it was the Martin Luther King episode, or the premiere, or Grandma Ida, or Sally actually catching Don, all of that was about the story of what is Don going to do? He wants to stop doing this. [His childhood] is the place to start. Ted even says it when he talks about sort of making a sacrifice, that the world is in such a mess. And then, of course, there is Mitchell, his mistress' son. The world is an open revolution in 1968, and ends with Richard Nixon as the president, and tanks rolling into Czechoslovakia, and a blood bath in Mexico City, and everything sort of gets tamped down. My analysis of it was that he's got to turn to the thing that he can control, and if there's a possibility of change there, that's outside all of that.

It seemed for a moment in the finale that he was going to escape again, but then the Hershey pitch sets him off. Why Hershey’s?The Hershey pitch was something I came in with at the beginning of the season, and I knew it would be Hershey. And I knew that we would spend time in the whorehouse and get a sense of where he was really from. It's not the carousel. He gives this speech. I mean, it's very personal and the audience knows that what he's saying is true. It just felt like, after the wreckage he has wrought with his lies and seeing Ted basically say, “I know you're a good man,” that it was time to come clean. That beautiful scene between Don and Megan where he says, “It got out of control — I got out of control,” I think that he is recommitting himself to her. And then the reality of the fact that Sally has changed her name and is drinking. Betty thinks it's because they got divorced; Don knows it's something else. I think there's so much shame there that it finally catches up with him and he realizes that he has to do this.

When you wrote that final moment between Don and Sally, did you do it thinking that things were going to get better for Don on a personal level?I honestly think that that act and that look that is exchanged so beautifully between those two actors is a moment that many of us have never even had in our life, and if nothing else, that moment in itself is an improvement. So is it the beginning of something? Who knows? The season started with Don saying, “I don’t want to do this anymore.” There is an indication that he doesn’t. I don’t know what to tell you beyond that. I hope that people feel the seriousness of the journey that we went on of questioning who Don is, and the repeated behavior, and the fallout from that.

There was some criticism midway through the season that Don’s behavior was starting to feel repetitive, or stagnant. What do you think when you read things like that, knowing how the season eventually plays out?Honestly, I don’t hear it. And the idea that there are cumulatively [millions] of viewers a week, and one person said that? The amount of criticism that goes on is purely flattering. It shows an investment. The idea that anything is stagnant in this show, unless we are saying it's stagnant because the story is that Don's life is stagnant, that's a ludicrous criticism to me. But I don’t hear it. I will be honest with you. It's like a secret club sometimes, this show. The idea that we are at 80 episodes and told this fresh new story, I think the audience appreciated it. They appreciated us playing with the form. They appreciate that we are playing with genres because we don’t really have one. I've never had a more positive experience when the show was on the air than I have this year. I'm not kidding. I'm including everything.

There were so many conspiracy theories this season! Is Bob Benson a government spy? Is Megan going to die? Is she already dead? Why do you think the show inspired all that this time?I don’t know. Again, it's flattering. If I was smart and I was really Don Draper, I would find a way to plant those things so people would talk about the show. The fact that it happens naturally is thrilling to me. I'm still lingering on the idea that people were critical of the show. You know, the show has been out there for a long time now and there are huge expectations on it. And we start the story fresh every year and there's always resistance because people feel a sense of ownership. So sometimes they think they should be writing the show. Where we take it is where it needs to go. And whether it was the premiere this year, which really explored how we're seen from the outside world; Megan's miscarriage right away; the use of the soap opera; Sylvia and what she meant to Don; Don's obsession with Sylvia; Peggy's lack of choices; the Martin Luther King assassination; Don's realization about his relationship with his kids; people being driven closer together ... The merger — I mean, that's episode five. So I don’t even know what to tell people. I feel very proud of the big events of this season, which are, honestly, where Don is, and where Don and Megan are, and Sylvia, the introduction of the chaos of the world in 1968, the merger, then Don reuniting with Betty, his obsession with and rejection by Sylvia, being discovered by Sally, trying to crush his partner, and eventually reconciling with himself. I don’t know what more you can do in twelve weeks of TV.

The mystery of Bob is one viewers really latched on to. Can you talk a little bit about why you teased him out the way you did?We're always looking at the management structure of the agency like it's a real business. And our feeling was that Pete would, at this point, be really at the top of his game at the beginning of the season. His interaction with Don in the premiere — you've never seen him that calm, and that in charge, and that clear on what his profession is. His disintegration over the season, a lot of it had to do with sort of seeing his job through the eyes of Bob. We wanted him to have a protégé, and my feeling was that Pete is very admirable to somebody. Who is that person? The characters of Don and now Bob are drawn from what I think is the story of American success. We are very tolerant of a certain kind of, let's put it this way, unsubstantiated achievement. And the fact that Bob has merit in his job, a lot of it comes from the fact that he's a chameleon. It really, really works in this business environment. I just love that, over the course of the season, we would see that Pete had learned something. And that he knew, after all this time, even though he didn't learn how to deal with his marriage, didn't learn how to deal with his mother, all the problems that he's had and been carrying around, he had learned not to mess with someone like Bob.

Until he does in Detroit and gets burned.Unfortunately, he couldn't contain himself. But the show is about underdogs and Bob is another underdog. I feel like the show itself is an underdog. It's part of why there's room for so much conversation and argument, and why there's 18-year-olds talking to their grandparents, and husbands and wives either having sex or fighting after they watch the show. Your allegiances are constantly being switched based on the idea that everybody has a reason for why they're doing what they do. And who among us has not done something really bad. On this scale, too. You know what I mean? It's not murder.

The finale ends, for me, on a lot of hopeful notes for a lot of these characters. Relationships on the mend between Pete and Trudy, and Joan and Roger. Peggy’s alone but she’s also on the rise professionally. As you head towards the final season, do you feel like you have you grown attached to these characters in a way that it impacts the way their stories will end? Could you really not give Peggy some sort of happy ending?Here's the challenge of the final season: It's not just an ending of a season; it's the ending of the show. I haven’t really thought about it. I've always taken this one season at a time, and we tell the story. I and the writers get a sense of how it's going to end [before each] season. Because [in season six] we're also telling the story of 1968, and 1968 is a lot like Don [in the sense that] even if he could get away with returning to normal, that was not enough. He actually had to have at least a small breakthrough. That's where that came from. In terms of how it works season to season, I never know what's dark. I couldn't believe that people felt “Shut the Door, Have a Seat” had a hopeful ending. I mean, Betty was going to get divorced, Don was moving out alone to the Village, the song "Shahdaroba" is playing, the children are alone with the housekeeper. I'm always looking for something that's beyond words because I'm not a critic. I'm trying to express something. It's always a mixed bag, just like life. That's the pleasure of doing the show. And the last season has got to end the whole thing, so it's an extra thing on top of it. And I may just punt and just deal with the season as itself and hope that is resonates.

Peggy says she didn’t have choices this season. Can she have a happy relationship?That’s something that we talk about all the time and the story of this season for her was that she did not have any choices. Every decision was made for her. Whether it was who she was going to work for, where she was going to live, who she would have a relationship with. Even her business life was completely out of her control. And even when she has the conversation with Joan, when Joan brings in Avon, you're seeing someone who has really grown as a businessperson and trying to face reality. So yeah, her personal life has been a disaster. I don’t know what to tell you. Sometimes it's the secret of doing great creative work.

Here are a few things that happen in 1969: the Moon landing, Woodstock, the FCC's ban on cigarette advertising on television and radio. Have you begun to think about things that you're going to deal with?No. And I don’t know if we're going to come back [in 1969]. I don’t know anything yet. I literally have to stop thinking about it, let the finale play out, and really get my head blank. For me, I was sort of dreading dealing with 1968 because it was kind of, on some level, the climax of the '60s and everything that I was making the pilot about. The pilot of the show was kind of about, Can you imagine that in eight years that's what the world will be? The fact that we've gotten to go on this journey with these people is in itself an incredible experience, and 80 episodes into it, I'm thinking more about the people and the timelessness of that journey. I never really start with the year. The events are intimidating usually and I don’t want it to be a history lesson. I don’t want people just checking things off in their book. Although, you know, I love that you're curious about how we're going to handle it.

Megan appears to be done with Don, and it feels permanent because, unlike Betty, she has no kids with him. Does Megan have a future with the show?Well, I mean, it certainly looks bad, and she does say, "I can't take this right now." But what is she? I think there's just a moment of realization that Jessica [Paré] just hit out of the park. We were talking about the scene [and she asked], "Is this a tearful experience?" No, it's angry. Where she looks at [the situation] and she realizes, Oh, my god, I have been helping someone who is really not looking out for my best interests. And she's the most modern character on the show to me. She really is. I love that her job is so important to her and I love that she is sort of skating the traditional wife thing. She is not Betty Draper, or Joan, or even Peggy in terms of her concept of what the traditional wife is. So for me, it was literally just like the partners putting Don on leave. At a certain point, [everyone's] like, "Really? Forget it." And that's what her use of profanity is about also. I think that that's the first time we've heard a woman say that on the show.

Peggy said the f-word once when that guy was re-enacting that bit on The Tonight Show.I guess it's the second one then. There — Megan’s in good company. [Cursing] has been part of the evolution of the show because I've wanted to show it coming into the culture more. It's about the language of the culture and the network has been great about letting me dip it in. You don’t hear it, but people know it's there, and that has shock value, which [actual cursing] really doesn’t any more. But, back to Megan, I feel like we left her in a place where she's had a realization.

Ted and Pete are going to California. Megan has lined up meetings there. Is it possible for the show to be bi-coastal next year?We have no idea when we're coming back in the story. And my take on it is: I haven’t really thought about it. All I can say is, when Don divorced Betty, everybody thought that we'd never see her again. No matter whether they're in California or not, these characters are part of our story.

Viewers seemed to have softened on Betty, coincidentally, when the character herself appears more content than she’s ever been.I look at that phone call in the finale — I got to be there and direct January. Probably her great moment [of the season] is, of course, that scene in bed in episode nine. But that phone call with Don? I'm just sitting there watching everything go on in her head. Look at it all together: the stuff in the car with Sally, that moment with the admissions lady at Miss Porter's where she says, “It's tough to raise a young lady, let alone be one.” I just feel like January brings this, for want of a better word, this weight of the reality of someone who is maturing. I don’t know if Betty’s learned anything. I just felt that her whole frustration with her failure ... anybody who's ever wondered if she is really a mother to those children can hear it in that moment on the phone. And that was all January.

Vincent Kartheiser said that you personally demonstrated how Pete should fall down the stairs in “For Wide Release." True?There are always stunt issues and I never ask them to do anything that I wouldn’t do myself. You don't want somebody to get injured. We did shoot it with a double, but that is Vincent that ended up in the show. Because I did [the fall] three times and did not have any injuries, I think he knew he could [pull it off]. I wanted it to look like he'd slipped and it had to be small enough that he could recover. What's so funny to me about it is that he falls and it's totally humiliating but he gets up like nothing happened.

Pete's alone, his mom is gone, and he's out of the Chevy account. But, like Don, he seems to have reconciled with his personal situation.That moment between him and Trudy in the finale, when she goes, “Now you're free,” and he says, “This is not the way I wanted it,” and she says “Now you know that" — like, talk about the whole season hitting you in the face. Like, Oh, right! I screwed up! Who does not identify with that?

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